methyl ((S)-2-(2-(1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-methyl-1-oxopropan-2-yl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-4-yl)propylamino)(3-(pyridin-4-yl)pyrrolidin-1-yl)methylenecarbamate | 1000819-13-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl ((S)-2-(2-(1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-methyl-1-oxopropan-2-yl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-4-yl)propylamino)(3-(pyridin-4-yl)pyrrolidin-1-yl)methylenecarbamate
• 英文别名: methyl N-[N-[(2S)-2-[2-[1-(7-azabicyclo[2.2.1]heptan-7-yl)-2-methyl-1-oxopropan-2-yl]-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-4-yl]propyl]-C-(3-pyridin-4-ylpyrrolidin-1-yl)carbonimidoyl]carbamate
• CAS: 1000819-13-5
• 化学式: C₃₉H₄₈N₆O₃S
• 分子量: 680.915
• InChiKey: LBNVTKXFWRBTPJ-IEXYTZDRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  49
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  131
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-吡咯烷-3-基吡啶 、 在 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以63%的产率得到methyl ((S)-2-(2-(1-(7-aza-bicyclo[2.2.1]heptan-7-yl)-2-methyl-1-oxopropan-2-yl)-5-(3,5-dimethylphenyl)-6H-thieno[2,3-b]pyrrol-4-yl)propylamino)(3-(pyridin-4-yl)pyrrolidin-1-yl)methylenecarbamate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of thieno[2,3-b]pyrroles as antagonists of the GnRH receptor

  摘要：

  A new class of small-molecule GnRH antagonists, the thieno[2,3-b]pyrroles, was designed. Herein, the synthesis and structure-activity relationships are described. Substitution at the C4 position was investigated; during this study, it was observed that introducing piperazines and piperidines improved the physical properties of the compounds while retaining good in vitro potency. This exploration led to the discovery of amidopiperidines with improved pharmacokinetic properties. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.09.099

文献信息

• Synthesis and structure–activity relationships of thieno[2,3-b]pyrroles as antagonists of the GnRH receptor
  作者：Jean Claude Arnould、Bénédicte Delouvrié、Pascal Boutron、Al G. Dossetter、Kevin M. Foote、Annie Hamon、Urs Hancox、Craig S. Harris、Mike Hutton、Maryannick Lamorlette、Zbigniew Matusiak

  DOI：10.1016/j.bmcl.2007.09.099

  日期：2007.12

  A new class of small-molecule GnRH antagonists, the thieno[2,3-b]pyrroles, was designed. Herein, the synthesis and structure-activity relationships are described. Substitution at the C4 position was investigated; during this study, it was observed that introducing piperazines and piperidines improved the physical properties of the compounds while retaining good in vitro potency. This exploration led to the discovery of amidopiperidines with improved pharmacokinetic properties. (c) 2007 Elsevier Ltd. All rights reserved.